Sodium hydride → 5-Bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile

HRID 534056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534056
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]([N+]([O-])=O)[C:16]([C:19]#[N:20])=[N:17][CH:18]=1.[NH4+].[Cl-]>O.CN(C=O)C>[Br:12][C:13]1[CH:14]=[C:15]([O:8][C:7]2[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][C:6]=2[CH3:9])[C:16]([C:19]#[N:20])=[N:17][CH:18]=1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27696985-Bromo-3-nitropyridine-2-carbonitrileHCID 150473662,4-Dimethyl-3-hydroxypyridine

Produkt 1

HCID 674859525-Bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrileAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A flask was charged with 2,4-dimethylpyridin-3-ol (9.0 g, 73.1 mmol) and DMF (80 mL) was added. Sodium hydride (2.03 g, 80.4 mmol) was added and the reaction was stirred for 15 minutes. 5-Bromo-3-nitropicolinonitrile (16.7 g, 73.1 mmol) was added and the reaction was stirred for 25 minutes. The reaction mixture was poured into 600 mL saturated NH4Cl and 600 mL water and then filtered, washed with water and a small amount of hexanes, and dried over high vacuum to provide 5-bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile (20.5 g, 67.4 mmol, 92.2% yield) as a light tan solid.

Aufarbeitung

  1. additionwas added
  2. stirringthe reaction was stirred for 25 minutes
  3. filtrationfiltered
  4. washwashed with water
  5. dry with materiala small amount of hexanes, and dried over high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6a5adb6877ee4547bb07c0e4688aef60
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853409B2

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